Best to do is prolly create main sections, then sub sections, then if necessary sub-sub sections, then periodically (after initial organization) ensure content is in the right category.
For example:
Outpost 2 Single Player ->Strategy (Eden/Plymouth strategies from Sierra, both are still valid)
Outpost 2 Multi Player -> Strategy (Lev's Pie building/Tech orders)
-> Map List (c_mpdata, added by sierra, contains information on most of the defualt maps, along with modes available for each associated map and a picture of the map along with its size. *NEEDS TO BE UPDATED)
Outpost 2 General Information -> Tales from New Terra, Story, ect.
Outpost 2 Help Game Help. Install problems and common fixes (such as to get the buttons to work correctly in the menu system) as well as multiplayer Help.
Obviously some sections can link to eachother fairly easily. An OP1 group should also be made available, and possibly even a Projects list.
Obviously, because I took the time to diagram this out, I'm in favor of keeping the Wiki.